CN114560848A - Reactive light/light-perspiration resistant composite color fastness improver and preparation method thereof - Google Patents
Reactive light/light-perspiration resistant composite color fastness improver and preparation method thereof Download PDFInfo
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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Abstract
The invention discloses a reactive light-resistant/light-sweat composite color fastness improver and a preparation method thereof; the structural formula is as follows:
the reactive light/light-sweat resistance composite color fastness improver can form covalent bond combination with cotton fibers, simultaneously realizes the functions of reducing textile ultraviolet irradiation and providing weak oxidizing atmosphere, inhibits the occurrence of dye photooxidation and photoreduction reaction on the cotton fibers, and realizes the lasting light/light-sweat resistance composite color fastness improvement effect on cotton fabrics dyed by reactive dyes.
Description
Technical Field
The invention relates to a reactive light-resistant/light-sweat composite color fastness improver and a preparation method thereof.
Background
Light fastness of dyed textiles refers to the ability of dyed fabrics to retain their original color under the action of sunlight. The light and sweat resistance composite color fastness refers to the capability of the dyed fabric to keep the original color under the combined action of sunlight and sweat. Both are important indexes for quality detection of dyed textiles. In current textile ecology, light and sweat resistance composite color fastness is a world-level problem. For the reactive dye dyed cotton fabric, after the fabric is worn outdoors for a period of time, parts of the back, collar and the like of the garment, which are in contact with a large amount of sweat of a human body, are easy to fade or discolor after being irradiated by sunlight, which is caused by poor light-sweat resistance composite color fastness of the garment fabric, not only is the appearance effect of the garment affected, but also certain threats exist on the health of the human body due to the photodegradation products of the dye.
The photobleaching mechanism of dyes is related to the light source, the dye structure and the type of dyed fiber. Ultraviolet rays in sunlight are the main cause of dye fading. In terms of the dye structure, if more electron donating groups exist in the molecular structure of the dye, the electron cloud density of a chromophore is increased, so that the dye is easy to photooxidize and fade; if more electron-withdrawing groups are present in the molecular structure of the dye, the electron cloud density of the chromophore is reduced, resulting in a dye that is more prone to photoreduction discoloration. Another study showed that reactive dyes are mainly photooxidized on cotton fibers, but mainly photoreduced on protein fibers. This is because proteins themselves have reducing properties and are liable to cause photoreductive fading of dyes. In the test standard of light-sweat resistance composite fastness, sweat composition contains reducing substances such as histidine, lactic acid and the like, so that the photoreduction reaction is the main cause of fading of the dyed cotton fabric under the condition of sweat.
Textile scientists have attempted to photostabilize and modify dyed cotton fabrics with reactive UV absorbers in an attempt to improve the light and sweat fastness of the complex from the standpoint of reducing the intensity of the available light radiation of the dye in the cotton fabric, and have found limited effectiveness. So far, there are few reports on effective solutions for simultaneously improving the light and light-sweat resistance complex color fastness of reactive dye dyed cotton fabrics. Therefore, there is an urgent need in the printing and dyeing industry to develop a reactive light/light-perspiration complex colour fastness enhancer capable of forming a durable protection with cotton fibres.
The invention of CN202110470679.0, entitled "reactive light-resistant and sweat-resistant complex fastness improver and a preparation method thereof", reports that a water-soluble compound I (i.e., intermediate M1) containing a dichloro-s-triazine reactive group and a weak oxidative nitro group can improve the light-resistant and sweat-resistant complex color fastness when applied to c.i. reactive black 5 dyed cotton fabric, but does not mention the improvement of the light-resistant color fastness.
Disclosure of Invention
The invention aims to provide a reactive light/light-sweat resistant composite color fastness improver and a preparation method thereof.
In order to solve the above technical problems, the present invention provides a reactive light/light-sweat resistance composite color fastness enhancer, the molecular structure of which contains ultraviolet absorption segments (benzotriazole derivatives), water-soluble groups (sodium sulfonate), weak oxidizing groups (nitro groups), and reactive groups (monochlorotriazine reactive groups), and the structural formula of which is as follows:
the invention also provides a preparation method of the reactive light/light-sweat resistance composite color fastness improver, which is characterized in that 2-amino-5-sodium nitrobenzenesulfonate and cyanuric chloride are used for preparing an intermediate M1 through a condensation reaction, and then the intermediate M1 is reacted with an amino-containing benzotriazole ultraviolet absorbent M2 (CAS: 139723-57-2) to prepare the reactive light/light-sweat resistance composite color fastness improver, and the specific steps are as follows:
1) Adding a proper amount of crushed ice, 92g of cyanuric chloride and water into a three-neck flask, and uniformly stirring in an ice bath (about 25-35 min); dropwise adding a 2-amino-5-sodium nitrobenzenesulfonate aqueous solution (the using amount of water is about 1L) prepared by 145-150 g of 2-amino-5-sodium nitrobenzenesulfonate, controlling the temperature to be 0-5 ℃ in the dropwise adding process, reacting under the conditions of stirring and ice bath after the dropwise adding is finished, adjusting the pH to be 5-6 (adjusting by using sodium hydroxide) in the reaction process, and reacting for 5-7 hours;
after the reaction is finished, carrying out acid precipitation (36-38% hydrochloric acid), filtering, and carrying out vacuum drying on the obtained filter cake to obtain an intermediate M1;
2) dissolving the intermediate M1 in deionized water to obtain a M1 solution; then dropwise adding an M2 aqueous solution, reacting the formed reaction system at 35-40 ℃ for 3-5 hours, and controlling the pH of the reaction system to be 6-7 in the reaction process; m1: m2 is 1:1 molar ratio;
m2 is benzotriazole ultraviolet absorbent containing amino (CAS: 139723-57-2);
after the reaction is finished, salting out, cooling and suction filtering are carried out, and a filter cake is dried in vacuum, so as to obtain the reactive light-resistant/light-sweat composite color fastness improver LS 1.
The step 2) is specifically as follows:
116.4g of intermediate M1(0.3mol) was placed in a three-necked flask, and 100ml of deionized water was added thereto and stirred. 98.4g M2(0.3mol) was weighed, a little deionized water was added, and sodium carbonate was added until all M2 was dissolved. Gradually dropwise adding the M2 solution into a three-neck flask dissolved with M1, controlling the pH to be 6-7, controlling the temperature to be 35-40 ℃, and reacting for 3-5 hours.
After the reaction is finished, NaCl salting-out dye is added for a few times at the constant temperature of 35 ℃, after the dye is fully separated out, the mixture is cooled and filtered, and the obtained filter cake is dried in vacuum, thus obtaining the reactive light/light-sweat composite color fastness improver LS 1.
The reaction equation is shown in formula 1.
In the invention, the ultraviolet absorption segment can absorb high-energy ultraviolet rays and reduce the activation of the dye by the ultraviolet rays in sunlight, thereby inhibiting the dye from generating photochemical reaction; the nitro with weak oxidizability can resist reducibility of histidine, lactic acid and other components in sweat and inhibit photoreduction reaction of the dye under the condition of light sweat, so that light fastness and light-sweat fastness of the cotton fabric dyed by the reactive dye are improved; the water-soluble group can enable the composite color fastness improver to be used for dyeing and finishing cotton fabrics together with reactive dyes with water solubility in a water system; the reactive group has the function of enabling the composite color fastness improver and the cotton fabric to be integrated through covalent bonding, and the washing fastness of the composite color fastness improver is improved.
The invention finds that the effective radiation rate of ultraviolet rays to the dye can be reduced and the reduction fading of the dye caused by reducing substances in sweat under the condition of light sweat can be resisted by simultaneously endowing the cotton fiber with certain ultraviolet absorption capacity and weak oxidation capacity, so that the light/light sweat resistance composite color fastness of the dyed cotton fabric is improved.
According to the invention, a sodium sulfonate water-soluble group, a benzotriazole segment with an ultraviolet absorption function and a monochlorotriazine active group are simultaneously introduced into the structure of a weak oxidizing substance nitrobenzene, so that the ultraviolet absorbent is endowed with weak oxidizing property, good water solubility and reactivity with cotton fiber hydroxyl, and when the ultraviolet absorbent is applied to cotton fabrics, the ultraviolet absorbent can be finished by a water bath method and forms firm covalent bonding with cotton fibers. The ultraviolet absorption segment can absorb ultraviolet rays, the activation of ultraviolet rays to the dye in sunlight is reduced, the nitryl with weak oxidizability can resist the reducibility of histidine, lactic acid and other components in sweat, and the photoreduction reaction of the dye under the condition of light sweat is inhibited, so that the light fastness and the light-sweat fastness of the reactive dye dyed cotton fabric are improved.
In conclusion, the reactive light/light-sweat resistance composite color fastness improver can form covalent bond combination with cotton fibers, simultaneously realize the functions of reducing textile ultraviolet irradiation and providing weak oxidizing atmosphere, inhibit the occurrence of dye photooxidation and photoreduction reaction on the cotton fibers, and realize the lasting light/light-sweat resistance composite color fastness improvement effect on the cotton fabrics dyed by the reactive dye.
Drawings
FIG. 1 is a graph of a dyeing or finishing process for cotton fabric with reactive dyes or reactive light/light-sweat fastness enhancers.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of protection of the invention is not limited thereto:
in the invention:
m2: amino-containing benzotriazole uv absorbers, CAS: 139723-57-2.
Example 1, a process for the preparation of a reactive light/light-perspiration complex colour fastness improver, successively following steps:
1) 50g of crushed ice, 92g of cyanuric chloride and 200mL of water were added to a three-necked flask, and the mixture was stirred in an ice bath for 30 min. 147g of 2-amino-5-nitrobenzenesulfonic acid sodium salt is dissolved in 1L of water and slowly dripped into a three-neck flask, the temperature is controlled to be 0-5 ℃ in the dripping process, and the dripping time is about 10 min. The dropwise adding process and the reaction process are carried out under the conditions of stirring and ice bath, sodium hydroxide is used for adjusting the pH value to be 5-6 in the reaction process, the reaction is finished after about 6 hours, acid precipitation (the concentration of hydrochloric acid is 36-38%, the using amount is 500ml) is carried out, filtration is carried out, the obtained filter cake is dried in vacuum (dried at 30 ℃) to constant weight, an intermediate M1 is obtained, and the yield is 81.3%.
Intermediate M1 is:
2) 116.4g M1(0.3mol) is put into a three-neck flask, 100ml of deionized water is added, and the mixture is stirred to obtain M1 solution. 98.4g M2(0.3mol) was weighed, a little deionized water (about 100ml) was added, and 12g sodium carbonate (the role of sodium carbonate was to adjust the alkaline pH and increase the water solubility of M2) was added until M2 was completely dissolved, resulting in a M2 solution.
And gradually dropwise adding the obtained M2 solution into a three-neck flask filled with the M1 solution, reacting at the temperature of 35-40 ℃ for 3-5 hours, and controlling the pH of a reaction system to be 6-7 in the reaction process (adjusting the pH value by supplementing a sodium carbonate saturated solution).
After the reaction is finished, NaCl (3 times, the total amount of NaCl is about 45g) is added into the mixture for salting out the dye for a plurality of times at the constant temperature of 35 ℃, so that the dye is fully separated out, the mixture is cooled to 20 ℃ and then is filtered, and the obtained filter cake is dried in vacuum to constant weight, so that the reactive light/light-sweat resistance composite color fastness improver LS1 (about 165.7g) is prepared, and the yield is 84.2%.
The reactive light/light-sweat resistant composite color fastness improver LS1 has the following structural formula:
1H NMR(400MHz,DMSO-d6)：δ10.35(s,1H),9.43(s,1H),8.95(s,1H),8.69(s,1H),8.42(d,1H),7.92(d,1H),7.82(m,2H),7.76(s,1H),7.63(d,1H),7.20(m,2H)；ESI MS(m/z,％):656.0([M-Na]-,100)。
the use of the reactive light/light-perspiration complex fastness improver LS1 according to the invention for dyeing cotton fabrics is described below by way of experiments.
Experiment 1, c.i. reactive black 5 was selected to dye cotton fabric, and the dyeing experiment was performed according to the following process recipe and process curve.
The dyeing process formula comprises: the dye dosage is 2% o.w.f, the sodium chloride is 40g/L, the anhydrous sodium carbonate is 10g/L, and the bath ratio is 1: 50. And taking out a sample after dyeing, and soaping for 10min in a water bath at 95 ℃, wherein the formula of the soaping liquid is 2g/L of soap flakes and 2g/L of anhydrous sodium carbonate. The dyeing process curve is shown in figure 1.
Experiment 2, LS1 obtained by the invention, an intermediate M1 and the following compounds I to V are applied to the post-treatment of C.I. reactive black 5 dyed cotton fabrics obtained by the experiment 1, and the light-resistant and light-sweat-resistant composite color fastness of dyed fabrics is evaluated.
Description of the invention: the LS1 of the invention simultaneously contains an ultraviolet absorption segment (benzotriazole derivative), a water-soluble group (sodium sulfonate), a weak oxidizing group (nitro group) and a reactive group (monochlorotriazine active group);
and, instead,
compound I lacks the weakly oxidizing group (nitro) relative to LS 1;
compound ii lacks the uv absorbing moiety (benzotriazole derivative) relative to LS 1;
compound iii lacks reactive groups (monochlorotriazine reactive groups) relative to LS 1;
compound IV replaces the benzotriazole uv absorbing moiety with a benzophenone uv absorbing moiety relative to LS 1;
Compound V altered the benzotriazole uv absorbing fragment structure relative to LS 1.
The post-finishing process specifically comprises the following steps:
1. aiming at the reactive light/light-sweat resistant composite color fastness improver LS1 and the compounds I to II, IV to V:
1.1), aiming at the C.I. active black 5 dyed cotton fabric obtained in the experiment 1, the usage amounts of reactive light-resistant/light-sweat composite color fastness improver LS1, the intermediate M1 and the compounds I-II and IV-V are all 3% o.w.f, the sodium chloride is 40g/L, the anhydrous sodium carbonate is 10g/L, and the bath ratio is 1: 50; and taking out the cloth sample after finishing, and drying and then soaping. The finishing process curve is the same as the dyeing process curve of the reactive dye on the cotton fabric in the figure 1;
each time of soaping is as follows: soaping in water bath at 95 deg.C for 10min, wherein the formula of soap lotion is 2g/L soap flake and 2g/L anhydrous sodium carbonate.
Drying the cloth sample directly obtained after finishing and the cloth sample washed for 5 times, and then respectively carrying out the following 1.2);
note: the above drying is drying at 80 ℃.
1.2) soaking the cloth sample in acid sweat 1 described in GB/T14576-.
1.3) and canceling the finishing in the step 1.1), directly performing the step 1.2) on the C.I. active black 5 dyed cotton fabric obtained in the experiment 1, and performing the step 1.2) on the C.I. active black 5 dyed cotton fabric obtained in the experiment 1 after performing the soaping for 5 times (the soaping method is the same as the step 1.1) and drying the same), wherein the steps are used as a comparison.
2. Because the structure of the compound II I does not contain active groups which react with cotton fibers, different finishing processes are adopted, and the method specifically comprises the following steps:
2.1) and each soaping comprises the following steps: soaping in water bath at 95 deg.C for 10min, wherein the formula of soap lotion is 2g/L soap flake and 2g/L anhydrous sodium carbonate.
Directly performing the following step 2.2) on a plurality of dyed cotton fabrics (each piece is 0.25g) with equal mass, or performing soaping for 5 times and drying and then performing the following step 2.2); the drying is drying at 80 ℃.
2.2) soaking the cloth sample in acid sweat 1 for 30min, then rolling off the redundant solution by using a padder, wherein the mangling rate is 100%, and then taking 1mL of compound III with the concentration of 10g/L to carry out liquid spraying finishing on the compound III. And then, carrying out a lighting experiment according to a GB/T14576-.
3. The cloth sample without sweat impregnation finishing is directly subjected to a light irradiation experiment according to the GB/T8426-1998 national standard method, and after the experiment is finished, the cloth sample is subjected to light fastness rating.
The light-sweat resistance composite color fastness and the light-fastness of LS1, the intermediate M1 and the dyed cotton fabrics finished by the compounds I-V and the unfinished dyed cotton fabrics are respectively compared, and the results after 5 times of soaping and unsaponifying are compared, and the results are shown in the table 1.
Table 1 shows that the light-sweat resistance composite color fastness and the light-color fastness of the dyed cotton fabric after I-V finishing and the unfinished dyed cotton fabric are M1, LS1 and I-V
As can be seen from table 1, compared with the unfinished fabric, the light and sweat resistance composite color fastness of the finished reactive light and sweat resistance composite color fastness improver M1 is improved from 2 grade before finishing to 4 grade after finishing under the conditions of acid sweat 1 and light, but the light and sweat resistance color fastness is still 4 grade, and is not improved. The M1 structure only has weak oxidative nitro, can inhibit the photoreduction fading of the dye, can only improve the light and sweat resistance composite color fastness, but has no obvious effect on improving the light resistance color fastness of the dyed cotton fabric.
After finishing the reactive light-resistant/light-sweat composite color fastness improver LS1, under the conditions of acid sweat 1 and illumination, the light-sweat resistance composite color fastness is improved from 2 grade before finishing to 4 grade after finishing, which shows that LS1 can obviously improve the light-sweat fading resistance and discoloration resistance of the reactive dye dyed cotton fabric. After the reactive light/light-sweat resistant composite color fastness improver LS1 finished fabric is soaped for 5 times, the light-sweat resistant composite color fastness is still 4 grade, which shows that LS1 and cotton fiber form stable covalent bond combination and the washing fastness is excellent. In addition, the light fastness is improved from 4 grade to 5-6 grade, and the effect is very obvious.
The light and sweat resistance composite color fastness after the compound I is finished is also improved to a certain degree, and can be improved from 2 grade before finishing to 3 grade after finishing, but the improvement effect is not as good as LS 1; the improvement of light fastness is improved from 4 grades to 4-5 grades, and the improvement effect is not as remarkable as LS 1. The compound II is finished, the light-sweat resistance composite fastness is improved from 2 grade before finishing to 3 grade after finishing, while the light-sweat resistance composite fastness can be improved to 4 grade, and the compound II is obviously lower than that of the compound II; the light fastness of the product is not obviously improved and is still 4 grade. The above results indicate that the ultraviolet absorbing segment and the weakly oxidizing segment, when acting alone, have a limited effect on improving the light-sweat complex fastness and light-color fastness of the dye.
The light-sweat resistance composite color fastness of the fabric finished by the compound III is improved from 2 grade to 3-4 grade, the effect is obvious, but the light-sweat resistance composite color fastness is reduced back to 2 grade after 5 times of washing. Indicating that the compound III without active group can not be combined with the cotton fiber in reactivity and has poor washing fastness.
The light-sweat resistance composite color fastness of the fabric finished with the compounds IV and V is respectively improved from level 2 to level 3 and 3-4, the improvement effect is general, after the fabric is washed for 5 times, the light-sweat resistance composite color fastness is still level 3 and 3-4, and the washing fastness is good; the color fastness to light is improved by about 1.0 grade; the improvement effect of the light-sweat resistance composite color fastness and the light-color fastness of the compounds IV and V are not as good as that of LS 1. The above results indicate that not all compounds containing ultraviolet absorbing fragments and weakly oxidizing functional fragments have excellent light-sweat complex color fastness and improvement effect of light-fastness, and structural screening is required.
In conclusion, the LS1 structure has ultraviolet absorption and weak oxidation functions, has a remarkable synergistic effect in the aspect of improving light and sweat resistance composite color fastness, and also has a good effect in the aspect of improving light fastness.
Finally, it is also noted that the above-mentioned list is only a few specific embodiments of the present invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (3)
1. A reactive light/light-sweat resistant composite color fastness enhancer characterized by the structural formula:
2. a process for preparing a reactive light/light-sweat fastness enhancer according to claim 1, characterized in that: 2-amino-5-nitrobenzenesulfonic acid sodium salt and cyanuric chloride are subjected to condensation reaction to prepare an intermediate M1, and then the intermediate M1 is reacted with an amino-containing benzotriazole ultraviolet absorbent M2 to prepare the reactive light/light-sweat resistance composite color fastness improver.
3. A process for the preparation of a reactive light/light-sweat complex colour fastness enhancer according to claim 2, characterized in that it comprises the following steps:
1) Adding ice water and 92g of cyanuric chloride into a container, uniformly stirring in an ice bath, dropwise adding a 2-amino-5-nitrobenzenesulfonic acid sodium sulfonate aqueous solution prepared from 145-150 g of 2-amino-5-nitrobenzenesulfonic acid sodium salt, controlling the temperature to be 0-5 ℃ in the dropwise adding process, reacting under the conditions of stirring and ice bath after the dropwise adding is finished, adjusting the pH to be 5-6 in the reaction process, and reacting for 5-7 hours;
after the reaction is finished, carrying out acid precipitation and filtration, and carrying out vacuum drying on the obtained filter cake to obtain an intermediate M1;
intermediate M1 is:
2) dissolving the intermediate M1 in deionized water to obtain a M1 solution; then dropwise adding an M2 aqueous solution, reacting the formed reaction system at 35-40 ℃ for 3-5 hours, and controlling the pH of the reaction system to be 6-7 in the reaction process; m1: m2 is 1:1 molar ratio;
m2 is an amino-containing benzotriazole ultraviolet light absorber;
after the reaction is finished, salting out, cooling and suction filtering are carried out, and a filter cake is dried in vacuum, so as to obtain the reactive light-resistant/light-sweat composite color fastness improver LS 1.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117051592A (en) * | 2023-08-25 | 2023-11-14 | 广东瑞源科技股份有限公司 | Preparation method of ultraviolet-proof fabric |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03241069A (en) * | 1990-02-15 | 1991-10-28 | Sumitomo Chem Co Ltd | Hydroxybenzotriazole compound and dyed fiber material, containing the same fixed thereto and fast to perspiration and light |
| US5502174A (en) * | 1993-09-01 | 1996-03-26 | Bayer Aktiengesellschaft | Reactive dyestuffs based on a substituted barbituric acid |
| CN101880470A (en) * | 2010-03-02 | 2010-11-10 | 浙江吉华集团有限公司 | Benzotriazole reactive dye for resisting ultraviolet radiation and preparation method thereof |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03241069A (en) * | 1990-02-15 | 1991-10-28 | Sumitomo Chem Co Ltd | Hydroxybenzotriazole compound and dyed fiber material, containing the same fixed thereto and fast to perspiration and light |
| US5502174A (en) * | 1993-09-01 | 1996-03-26 | Bayer Aktiengesellschaft | Reactive dyestuffs based on a substituted barbituric acid |
| CN101880470A (en) * | 2010-03-02 | 2010-11-10 | 浙江吉华集团有限公司 | Benzotriazole reactive dye for resisting ultraviolet radiation and preparation method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117051592A (en) * | 2023-08-25 | 2023-11-14 | 广东瑞源科技股份有限公司 | Preparation method of ultraviolet-proof fabric |
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